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Showing NP-Card for Monoethyl malonic acid (NP0000603)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-09-03 04:22:27 UTC
NP-MRD IDNP0000603
Natural Product DOIhttps://doi.org/10.57994/2867
Secondary Accession NumbersNone
Natural Product Identification
Common NameMonoethyl malonic acid
DescriptionMonoethyl malonic acid is an organic acid identified in the urine in a healthy pediatric population. (PMID 14708889 ).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0000603 (Monoethyl malonic acid)

Ethyl Malonate.mol
  Mrv1652305271900222D          

  9  8  0  0  0  0            999 V2000
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  8  9  1  0  0  0  0
  5  8  1  0  0  0  0
M  END
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3D MOL for NP0000603 (Monoethyl malonic acid)

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3D SDF for NP0000603 (Monoethyl malonic acid)
Ethyl Malonate.mol
  Mrv1652305271900222D          

  9  8  0  0  0  0            999 V2000
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  1  0  0  0  0
  8  9  1  0  0  0  0
  5  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000603

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)

> <INCHI_KEY>
HGINADPHJQTSKN-UHFFFAOYSA-N

> <FORMULA>
C5H8O4

> <MOLECULAR_WEIGHT>
132.1146

> <EXACT_MASS>
132.042258744

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.28606993404516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-ethoxy-3-oxopropanoic acid

> <ALOGPS_LOGP>
0.01

> <JCHEM_LOGP>
0.17158474233333318

> <ALOGPS_LOGS>
-0.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9170309395442535

> <JCHEM_PKA_STRONGEST_BASIC>
-7.1471073439128325

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
28.5055

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl hydrogen malonate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0000603 (Monoethyl malonic acid)
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PDB for NP0000603 (Monoethyl malonic acid)
HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Ethyl Malonate.mol                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.000  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   1.155   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.334  -1.155   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.667   1.155   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.001  -1.155   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -1.155   0.000  0.00  0.00           C+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3                                                       
CONECT    3    2    6    7                                                  
CONECT    4    1                                                            
CONECT    5    1    8                                                       
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    9    5                                                       
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0000603 (Monoethyl malonic acid)
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SMILES for NP0000603 (Monoethyl malonic acid)
CCOC(=O)CC(O)=O
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INCHI for NP0000603 (Monoethyl malonic acid)
InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)
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Synonyms
ValueSource
Monoethyl malonateGenerator
(Ethoxycarbonyl)acetateHMDB
(Ethoxycarbonyl)acetic acidHMDB
3-Ethoxy-3-oxopropanoateHMDB
3-Ethoxy-3-oxopropanoic acidHMDB
Ethyl hydrogen malonateHMDB
Ethyl malonateHMDB
Malonic acid ethyl esterHMDB
Malonic acid monoethyl esterHMDB
Monoethyl hydrogen malonateHMDB
Ethyl hydrogen malonic acidHMDB
Chemical FormulaC5H8O4
Average Mass132.1146 Da
Monoisotopic Mass132.04226 Da
IUPAC Name3-ethoxy-3-oxopropanoic acid
Traditional Nameethyl hydrogen malonate
CAS Registry Number1071-46-1
SMILES
CCOC(=O)CC(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)
InChI KeyHGINADPHJQTSKN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-06-18View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassDicarboxylic acids and derivatives  
Direct ParentDicarboxylic acids and derivatives  
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Carboxylic acid ester
    • 

  • Carboxylic acid
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point47 - 50 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility125 g/LALOGPS
logP0.01ALOGPS
logP0.17ChemAxon
logS-0.02ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.51 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000576  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022124  
KNApSAcK IDNot Available
Chemspider ID63783  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5558  
PubChem Compound70615  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References